Macrocyclic oxonium ylide formation and internal [2,3]-sigmatropic rearrangement. Catalyst influence on selectivity

被引：26

作者：

Doyle, MP

Peterson, CS

机构：

[1] Department of Chemistry, Trinity University, San Antonio

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(97)01160-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formation of 13-membered ring oxonium ylides and their subsequent stereocontrolled [2,3]-sigmatropic rearrangement to 10-membered ring lactones occurs in catalyst dependent competition with macrocylic cyclopropanation. (C) 1997 Elsevier Science Ltd.

引用

页码：5265 / 5268

页数：4

共 26 条

[1] [Anonymous], 1995, COMPREHENSIVE ORGANO
[2] Selectivity in the rearrangements of oxonium ylides
Brogan, JB
Bauer, CB
Rogers, RD
Zercher, CK
[J]. TETRAHEDRON LETTERS, 1996, 37 (29) : 5053 - 5056
[3] BRUCKNER R, 1991, COMPREHENSIVE ORGANI, V3, P813
[4] Stereoselective synthesis of the bicyclic core structure of the highly oxidised sesquiterpene neoliacinic acid
Clark, JS
Dossetter, AG
Whittingham, WG
[J]. TETRAHEDRON LETTERS, 1996, 37 (31) : 5605 - 5608
[5] MACROCYCLIC LACTONES FROM DIRHODIUM(II)-CATALYZED INTRAMOLECULAR CYCLOPROPANATION AND CARBON-HYDROGEN INSERTION
DOYLE, MP
PROTOPOPOVA, MN
POULTER, CD
ROGERS, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (27) : 7281 - 7282
[6] SYNTHESIS OF ALLENES BY [2,3]-SIGMATROPIC REARRANGEMENT OF PROP-2-YN-1-YL OXONIUM YLIDES FORMED IN RHODIUM(II) CARBOXYLATE CATALYZED-REACTIONS OF DIAZO-COMPOUNDS
DOYLE, MP
BAGHERI, V
CLAXTON, EE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) : 46 - 48
[7] Formation of macrocyclic lactones by enantioselective intramolecular cyclopropanation of diazoacetates catalyzed by chiral Cu-I and Rh-II compounds
Doyle, MP
Peterson, CS
Parker, DL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (12): : 1334 - 1336
[8] REARRANGEMENTS OF YLIDES GENERATED FROM REACTIONS OF DIAZO-COMPOUNDS WITH ALLYL ACETALS AND THIOKETALS BY CATALYTIC METHODS - HETEROATOM ACCELERATION OF THE [2,3]-SIGMATROPIC REARRANGEMENT
DOYLE, MP
GRIFFIN, JH
CHINN, MS
VANLEUSEN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) : 1917 - 1925
[9] FACILE CATALYTIC METHODS FOR INTERMOLECULAR GENERATION OF ALLYLIC OXONIUM YLIDES AND THEIR STEREOSELECTIVE [2,3]-SIGMATROPIC REARRANGEMENT
DOYLE, MP
BAGHERI, V
HARN, NK
[J]. TETRAHEDRON LETTERS, 1988, 29 (40) : 5119 - 5122
[10] A NEW AND EFFECTIVE METHOD FOR THE LOW-TEMPERATURE GENERATION OF SULFONIUM YLIDES FROM ALLYL SULFIDES
HARTLEY, RC
WARREN, S
RICHARDS, IC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (05): : 507 - 513

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